


A Man of Means

by vespirus



Category: Supernatural
Genre: Coming Out, F/M, Gay Bar, Gen, M/M, Pre-Series, Pre-Series Dean Winchester, Stanford Era, Trans Character, Trans Dean Winchester, Trans Male Character, Transitioning
Language: English
Status: Completed
Published: 2017-04-08
Updated: 2017-05-23
Packaged: 2018-10-16 05:58:38
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,231
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10565043
Author URL: https://archiveofourown.org/users/vespirus/pseuds/vespirus
Summary: That’s one scene he’ll always remember: Her smile and sparkling eyes and lilting voice focused on him as her beautiful fingers clicked cassette boxes together, Dean Martin singing about love and freedom through the tape deck, the fresh morning air sweeping past his open window as he drives them to a LGBT meeting.I'm a man of means by no means, king of the road...





	1. Chapter 1

**Author's Note:**

> whats up.. ive kind of lost my interest in taz and ive been not as into tf2 lately either so idk when ill update my other fics but heres A New One ...  
> thinking of another chapter or two based on the pilot and route 666 but otherwise not sure what else i want to do w this so open for suggestions !  
> [heres a spotify playlist following the songs mentioned in the fic if you want to listen along](https://open.spotify.com/user/shaedslayer/playlist/26iPzGiicSKpKhTLkmfrCo)

One of his only memories from  _ before _ is his music. His mother brushing his hair (his hair was long and her fingers soft, so gentle) with one of her albums playing in the background. The warm thrum of piano and bad audio and his strong voice crooning over the instruments.

He doesn’t think about it for years. Years and years. Not until Sam’s just walked out on him and his dad and he’s nursing a bad drink in a dim bar trying not to think about the twist in his dad’s voice when he told Dean that he’d call when he was ready to meet up again before he slung his bag over his shoulder and walked out on him too.

He’s picking at the label on his beer and listening to the low jazz crackling out of the shitty speakers when the same tune from that night, sitting on his mother’s bed, oozes into his ears. He swallows and taps on the bar to get the bartender’s attention. The man pulls another beer from under the bar with a too-warm smile.

“Another one for the lady?”

“What song is this?” His voice rasps disgustingly from the back of his sticky liquored mouth. The guy glances at the speaker nearby.

“Dean Martin. Think it’s called ‘Cry Like A Baby’ or something.”

He licks his dry lips and nods (and nods and nods. He’s pretty spaced out). The bartender moves on. He crosses his arms on the wet wood of the bar and lays his head down. He stays there until he feels too sick to stay. His heart is beating thick and warm in his chest by the time he sits in the driver’s seat of his car, not even the worn leather of the Impala helping.

He sleeps right there, wakes up with a crick in his neck and drives three hours to the first music store he comes across and buys all Dean Martin cassettes he finds.

He starts listening to them as he drives, pushes in tapes at random and lets it wash over him. It was a change from his usual music, but everything in his life was changing these days, so what was one more thing?

He ends up listening to them over and over. He finds himself tapping along on the steering wheel, humming softly along sometimes.

Sometimes he thinks about his mother. If she would be happy he reconnected with something she loved, something she gave him. He starts being able to smile at her memory alongside the pull in his chest that makes him want to pull into the nearest bar.

* * *

 

He didn’t really know why he kept his hair so short. At first it was because the memory of his mother was still too raw. He found it useful after that. Harder for monsters to grab onto, lighter, less maintenance, and pleasant in hot weather. And if there was another reason that he didn’t really understand, he didn’t have to explain. Not like anyone asked, of course. No one really seemed to notice. Or care.

But going unnoticed is a hunter’s job and being uncared for was better for everyone involved (considering the constant threat of death and all). And if there was one thing he thrived at, it was being a hunter.

* * *

 

Ever since Sam left to his better life, he and his dad had split up more often than not. They really only met up every now and then when one found a job that needed an extra hand. As much as Sam insisted he worshiped their father, he was honestly thankful for the time apart. Time to himself. He could finally clear his head, maybe think about who  _ he _ wanted to be.

All those years under his dad’s tutelage and he had no idea what he really wanted for himself or even what he liked. He liked his car and his cassettes and he liked lounging in the back of his car with his cassettes playing as he kissed someone attractive who thought he was attractive too. He was starting to really like Dean Martin.

Other than that, it was hard. Hard to pinpoint where his dad ended and he began. And it was scary. This wasn’t a scary that could be faced down with salt and fire though, so he avoided thinking about it directly.

He knew some stuff he didn’t like. He didn’t like being attacked, didn’t like being preached to, didn’t like fruity drinks, didn’t like being called “lady” or “girl”, didn’t like being treated like some pretty thoughtless thing.

He didn’t like it when the women he slept with called him a fellow lesbian, didn’t like it when the men growled in his ear calling him a dirty girl. The first he put down to being bi, not a lesbian, and the second to self-respect. He ignored the heady feeling in his chest when he thought about these things, though. Pushed people away when they said something wrong, pulled them closer when they finally shut up. It worked, most of the time.

* * *

 

He met Cassie when his dad called him in for help on a hunt. They wrapped it up pretty quickly together, and John left with barely a nod in his direction. It stung, but less than it might have before Sam left. His family was coming apart at the seams and he was almost too tired to care.

He stayed behind. Stayed for Cassie. They had hit it off, and everything about her pulled him in. The morning after, when he would usually make his excuses and split, he stayed. He watched her get dressed lazily from the bed, and when she sat down again and leaned over him he smiled into the kiss.

She brushed her fingers over his jaw and looked at him with something in her eyes. Something warm and gooey that made his heart shiver.

“Hey. I’m going to a LGBT meetup today. Wanna come?”

He would’ve said no, but a look into her eyes and his heart stuttered into his throat and pushed out a breathy “I’d love to.” The bright smile he’s rewarded with makes him sure this was the right answer.

He drives her, wants to show off the Impala. She loves it. She laughs and asks if he likes Dean Martin when she finds the collection of well-used tapes and he just grins back at her as the recording whistles out Gentle On My Mind.

(And that’s one scene he’ll always remember. Her smile and sparkling eyes and lilting voice focused on him as her beautiful fingers clicked cassette boxes together, Dean Martin singing about love and freedom through the tape deck, the fresh morning air sweeping past his open window as he drives them to a LGBT meeting.)

The meeting is interesting. He’d never gone to anything like it before. Never bothered. Something big and warm settled in his chest at the knowledge that everyone around him was like him in some way. Sort of like being in Harvelle’s. It was different, but they all were putting their lives on the line to face the truth in their own way.

They had a trans speaker who was working on writing a book about his transition. Cassie and everyone else listened warmly, supportive and attentive. As he listened, the sick heady feeling (the one that tied itself around his throat when people called him girly nicknames, the one from when girls spotted him and told him in relief that they were happy to find another woman there) reared its ugly head, and he excused himself to the bathroom.

He returned ten or twenty minutes later as the speech was winding down. Cassie glanced at him before he sat down. He wondered if she knew, if she could see it in his eyes, that he had been hiding in a stall and chewing on his fingers as he thought about some things he had never thought about before.

The people started to disperse, the room thinning out as he hung back next to the refreshment table and Cassie talked to some people she seemed to know. The speaker stays for a long time, shaking hands and talking about the book. Cassie’s occupied with catching up with some old friends, and he grabs a cookie and ducks his head and goes to talk to the speaker.

“Hi there,” the speaker, Chris, shakes his hand with a smile and the tightness in his chest loosens just a little. “What’d you think?”

“Good talk.”

“I saw you left for part of it. You alright?” Chris seems genuinely concerned and it’s disconcerting to have someone concerned over his comfort.

“Yeah, I just.. Yeah. Just made me think about some stuff.” Chris laughs sympathetically and pats his arm.

“Yeah, I’ve been there.”

There’s a beat of silence and he clears his throat.

“So.. Chris. How’d you pick that?”

“How’d I pick my name, you mean? I dunno. Took a while. I’ve seen some people who keep their birth name or just twist it a little but…That’s not for me. Ended up just thinking about stuff that’s important to me. My parents used to read Winnie the Pooh to me as a kid, so I ended up trying out Robin for a while. Like, Christopher Robin. I ended up going with Christopher in the end. It’s got good memories behind it.” Chris half-smiles at the memory and then gives him a searching look. “What about you?”

“Me? I, uh… Not really there yet. Not really anywhere yet.” Chris nods like he  _ get it _ , and he probably does. He glances back and Cassie catches his eye and nods towards the door. He takes the hint and turns to say goodbye to Chris to find Chris digging a card out of his jacket. He writes a number on the back and hands it over with an unreadable look.

“Hey, man.. I don’t even know what to call you,” Chris huffs a laugh.

“Uh, Winchester’s fine.”

“Winchester. Nice. Anyway, look. Winchester. If you ever need someone to talk to, call me. I’m usually free, being a writer gives me a lot of free time.” Chris says with a laugh, and he takes the card. He puts it in his inside pocket with a nod and a goodbye and leaves to drive Cassie back. He feels the card burning a hole in his pocket the entire way back.

The next couple of weeks are some of the best in his life. It’s hard, but Cassie’s so good to him, and there’s some sort of cathartic release to finally facing all this that’s been building up in the back of his head.

They go out for lunch the day after the meeting and the day after that they spend in Cassie’s small college apartment, listening to music and sitting so close that when he inhales he can smell the pomegranate shampoo off her bare neck.

He tells her then, slow and stumbling, dredging up things he’s buried so deep he forgot they existed until now. She listens so sweetly, watching him, focused totally on him. Holding his hands, wrapping herself up into his arms and kissing his neck and rubbing his hips as his voice trembles to match his hands. She pets his hair, his face, tells him she’s proud of him, that she loves him and she’s here for him through it all. She’s so, so careful with him. It’s dizzying in more ways than one -- letting out something bottled up so long, finally being truthful to himself, to someone else, having someone so honed in on him and making him feel safe and comforted. It doesn’t really make sense. Doesn’t fit together in his head, but he powers through it. He started this, he’s going to finish this.

They spend the evening curled up with each other in her too-small bed with wine and Dean Martin murmuring Buona Sera and he falls asleep with her head tucked under his and soft trumpets in his ears.

He tries out some different names. He thinks on Chris’s advice, looking through his meager possessions thoughtfully. He tries on Jimmy and James, but the possibility of the nickname Jim makes him decide against them. Jim’s too.. Normal. Next is Cliff, then Kirk, then Robert. Cliff and Kirk are close, he feels. Close, but no cigar. He’s pulling from the only things he knows: bands. Eventually it hits him as he’s pushing in another Best Hits cassette into the tape deck. He thinks on Martin for a few seconds, but no. It’s too dorky, doesn’t flow. Dean, though? Dean works.

Once he’s decided, he tells Cassie. She pulls him down for a long, long kiss, and by that evening he has her gasping his name over and over and damn if that isn’t the most beautiful sound he’s ever heard.

The last day he spends with her starts so well. He goes out and picks up muffins for breakfast as a surprise, whistling along to Ain’t That A Kick In The Head and breathing in the fresh air. He brings the muffins up to her room and knocks gently, opening it to find her still asleep where he left her. His heart feels so full at the sight and he knows he has to tell her. He can’t lie to her anymore.

It doesn’t go well. He leaves town. He leaves a card with his number at the bottom of a drawer with a note telling her it’s for “just in case.” He doesn’t think too hard about it. The cassette starts up on I’ve Grown Accustomed To Her Face when he hits play and he punches the eject button and tugs the tape out so hard he’s almost worried if he’s broken it.

* * *

 

He doesn’t talk to anyone for a while after that. He ends up meeting up with his dad for a hunt, a welcome break from his head and back to something that he’s used to. And maybe his dad calls him by his old name a couple times, but it’s usually pretty easy to avoid since there’s not much reason to say someone’s name when you’re talking to them.

He tries flirting a little the next time he stops at a gay bar, but all he gets is a woman sliding a hand into his jacket and telling him he’s a really hot butch before he pushes her away and slaps money down for his drinks and leaves.

He heads towards the north, going for the more open cities and ends up stopping in at a LGBT center for a trans support group. He doesn’t talk much and ends up with the suggestion to look into hormone therapy and he skips town with a pamphlet of doctors and clinics.

A few weeks later, he rolls out of the parking lot from his first testosterone shot to the tune of Bumming Around and the sun is in his eyes but he’s starting to really get what Martin means when he sings about living his life and doing as he likes.

* * *

 

He never got what Sam meant when he talked about there being more to life than hunting, that maybe he didn’t want to follow in their father’s footsteps, that maybe he wanted to make his own life and his own choices. When he looks into the mirror and finds the hairs on his face and his legs are starting to come out just a little thicker, just a little darker, he thinks he’s starting to understand.

He doesn’t know if his dad notices or not. He must, at some point, right? They meet up rarely and the changes are slow, so agonizingly slow, but after a few months his voice his deeper and his hair is thicker and he’s standing taller and he’s got new confidence and his dad must see something is different. He doesn’t say anything either way. But that’s just how his dad is. How he’s always been.

Who cares if Dean’s finally able to stand up straight, if he’s finally starting to actually enjoy being who he is, if he might finally be able to be somewhat happy? Who cares. It doesn’t matter. Hunting’s what matters. Not Dean.

* * *

 

He starts going to gay bars and LGBT meetings more. Maybe he and Cassie ended badly, maybe he’s scared of a lot of things now (commitment) because of that, but he can’t give up that feeling of community he got a taste of when he sat in a folding chair next to her and listened to Chris talk about how happy he is for the friends he’s made in the community.

The first one he goes into post-T (post-Cassie) he introduces himself as Dean in the lowest voice he can manage and the bartender gives him a knowing look and puts his first drink on the house. He stays there for a long while, leaving only after the last sounds of Quien Sera fades out from the speakers.

He starts keeping track mentally. When he rolls into a new town, he usually looks up to see if there’s anything happening while he’s there that he could stop by at. He makes note of towns that seem more accepting and which areas he should keep to himself in.

He finds himself beginning to be uncomfortable in normal bars, on edge and always looking over his shoulder. Like they all can see it, like they  _ know _ . He hustles pool and drinks and gets the hell out of there. He keeps hookups to gay bars and usually goes easier on the hustling there because he can’t bring himself to be unfeeling enough to the people there as he is in the grimy bars he usually hustles in.

He starts wearing binders when he can afford it (he doesn’t go running around in them because that would just make him slow and he could lose a few seconds of breath that might cost him his life) and eventually gets around to getting top surgery from a somewhat sketchy doctor and it’s a weight off his chest, in more ways than one.

After that and with the hormone therapy, it’s easier to stick to gay bars and LGBT meetups to find hookups. Just the thought of trying to explain his situation to someone he pulled out of a dingy roadside bar in the south makes his gut clench.

His dad  _ must _ notice by now after his surgery. He had always tried his best (even subconsciously) to hide his generous chest, but he had never cut a straight silhouette. He’s starting introducing himself as Dean, as John’s brother or son or associate. John still says nothing. Dean’s too tired to ask anymore.

* * *

 

His dad’s off on a hunt and he’s driving through a long wide open cross-country road. The windows are cracked and the winds flying through his short, short hair and Dean Martin is humbly declaring there’s no way he could be considered King of the Road and he taps the steering wheel and hums just to feel the deep vibration of it in his chest and thinks about if he would ever take up smoking.


	2. Chapter 2

He doesn’t really know what he’s thinking when he breaks into Sam’s house and wrestles him to the floor instead of just coming through the front door, but he’s not about to admit that. And really, if he  _ had _ just knocked or called, Sam would’ve just slammed the door in his face or not even picked up. This is probably the only way to actually get a conversation out of him.

It takes Sam a while to recognize him. Understandable, but he doesn’t really want to hash it out in front of Sam’s pretty girlfriend. So when Sam calls him by his old name, and Jess starts to ask if that’s the sister (that she’s probably heard nothing about), Dean cuts her off.

“Brother. Yeah. I’m good ol’ Sammy’s brother. Anyway,” Dean claps a hand on Sam’s back with more force than necessary and turns him towards the door, “I need to just have a chat with him. Privately. Family business, y’know how it is.” The girl bobs her head in a nod, her look of surprise not worn off yet. Sam’s too shell-shocked to protest as Dean steers them outside and closes the door behind them. He leans against the door to try and prevent Sam from immediately going back inside.

“Dad’s not been in contact with me for a long time. A  _ long _ time. I’ve got a bad feeling, Sam. I need your help.”

“I--What? Look, I’m done hunting. I told you.”

“Just this, man. He’s missing, and in some real trouble. If he’s not dead already. I can feel it.”

Sam gives him a withering look but Dean can’t let up on this. He can’t.

“I can’t do this alone.”

“Yes you can.”

Dean gulps and glances at his feet and rubs his hand against the short cropped hair on the back of his neck.

“Yeah well. I don’t want to. Okay?”

Sam’s mouth twists and he shuffles his feet. “What was he hunting?”

Dean doesn’t let out the sigh of relief he almost releases. Sam’s coming. Even if he says he’s not. Dean’s got him hooked in.

They talk shop, strike up an arrangement, and part ways.

Dean spends the rest of the night staring at the endtable in the crappy motel he’s staying in, listening to his walkman whisper Houston through his headphones, replaying the scene of Sam’s face when he realized what his older sister had become over and over in his head.

* * *

 

Af few months after starting T, he ended up in Stanford. He stood on the street, staring at the university campus for a few minutes until he turned away and ducked into a coffee shop. He munched on a croissant and looked through the large front window at the imposing school.

He didn’t really know why he was here. Well, he did, but. He wasn’t going to interrupt Sam’s perfect life. Ruin it with his weird shit. He wiped some crumbs off the table and sighed, not looking back up. Sam was probably acing everything. Well on his way to some high paying cushy office job or position in court or something, surely. Who was he to barge in and fuck everything up for him? With his cracking voice and scraggly facial hair and badly concealed chest.

He doesn’t hum along as On The Street Where You Live plays while he drives out of the city.

* * *

 

They’ve been on the road for a couple hours now. Dean staring resolutely ahead as Sam slouches silently in the passenger seat. The Black Sabbath cassette ends and Dean pops it out and shoves in another cassette in a practiced move without even glancing over. The first couple notes of Little Ole Wine Drinker, Me twang out of the speakers before he slams down the pause button. Out of the corner of his eye he sees Sam look at the tape deck and then at him. Dean works his jaw and tries to think of an excuse to mumble and switch tapes, but nothing comes, and he moves his hand off the tape deck and back to the wheel and they continue in silence.

For about a minute. Because Sam can’t let fucking anything slide.

“So…”

He trails off. Dean glances over at him shortly, feeling annoyed and more than a little defensive.

“What?” He asks flatly, since Sam didn’t continue.

“This.” Sam gestures at Dean in general and Dean flexes his hands on the wheel. “You’ve changed a lot since I last saw you.”

“Yeah, well. A lot’s happened since then.”

Sam snorts. “I’ll say.”

Sweet silence overtakes them for a couple beats until Sam has to say something again.

“Why didn’t you say anything? I mean.. to me. I would’ve been okay with it, you know.”

“Oh do I? Do I know? I didn’t know you’d kick me to the curb at the first real chance you got. I don’t know fucking anything about you anymore.” Dean tapped his foot on the accelerator moodily.

“You?”

“Me and dad, I mean.”

“It wasn’t about that. It was about having my own  _ life _ , s--dude. And that wasn’t gonna happen when I was hunting with you and drill sergeant Winchester.” Sam fidgeted in his seat and stared out the window.

“Sure. Whatever, man. I don’t care. Do whatever the fuck you want. After this, you’ll never have to see me again, and you can go to your fancy law school, and you can forget all about your freak family.” Dean ground his teeth and Sam wisely didn’t try to deny it. He was thankfully quiet for a bit more. Until,

“Did you get the surgery yet?”

“Look, let’s just fucking, not talk. Okay? Sound good? Good.” He went ahead and slapped play and fuck Sam and fuck keeping up with his old reputation and fuck everything. He scratched lightly on the wheel and muttered along under his breath. He could feel Sam shoot him a look when his voice cracked over “he asked who's the fool in the corner crying”. Fuck Sam. That’s just his body adjusting to the deeper voice. There’s not a meaning in everything.


End file.
